All Upcoming events

• Sat, 06 Dec, 2025 - 11:00 AM

  Winchester Winter Village

  Old Town Winchester Walking Mall

  4214+ Interested
• Sun, 14 Dec, 2025 - 11:00 AM

  Yuletide Mystical Market

  Raven Conjure

  1021+ Interested
• Sat, 06 Dec, 2025 - 10:00 AM

  Christmas Maker’s Market

  2502 N. Frederick Pike, Winchester, VA

  3233+ Interested
• Sat, 06 Dec, 2025 - 05:00 PM

  Follow The Star 2025 - Live Nativity Walking Tour

  Fellowship Bible Church

  2518+ Interested
• Fri, 05 Dec, 2025 - 05:00 PM

  Santa Pub Crawl — Downtown Winchester, VA

  15 E Boscawen st, Winchester, VA

  499+ Interested
• Fri, 12 Dec, 2025 - 08:00 PM

  Winchester Holiday Lights Trolley Tour

  1400 S Pleasant Valley Rd, Winchester, VA, United States, Virginia 22601

  217+ Interested
• Sat, 13 Dec, 2025 - 05:30 PM

  The Ghost of Christmas Past (A Paranormal Investigation)

  101 N Loudoun St, Winchester, VA

  74+ Interested
• Sun, 07 Dec, 2025 - 01:00 PM

  Holiday Wreath Making Workshop

  The Homestead Farm at Fruit Hill Orchard LLC

  USD 66
• Fri, 05 Dec, 2025 - 08:00 PM

  Cazhmiere @ Backseat Event Center w/Souled Out!

  Backseat Events

  40+ Interested
• Sat, 06 Dec, 2025 - 08:00 PM

  A Christmas Carol at Winchester Little Theatre Inc.

  Winchester Little Theatre Inc.
• Sat, 06 Dec, 2025 - 12:00 PM

  Winter Solstice Market at Winter Village

  125 S. Loudoun Street, Winchester, VA

  301+ Interested
• Sun, 07 Dec, 2025 - 04:00 PM

  Calypso Harp Duo: Songs of Light

  Grace Evangelical Lutheran Church, West Boscawen Street, Winchester, VA, USA

  Newly Added

  |

  Free
• Fri, 12 Dec, 2025 - 08:00 PM

  Cold Beer & Common Sense with Spencer Hatcher

  114 Full House Drive , Winchester, VA, United States, Virginia 22603

  114+ Interested
• Sat, 06 Dec, 2025 - 03:00 PM

  Adult Workshop: Holiday Wreaths

  901 Amherst St, Winchester, VA, United States, Virginia 22601

  36+ Interested
• Sat, 13 Dec, 2025 - 07:00 PM

  Fork In The Road @ Winchester Eagles!

  Winchester Virginia Eagles Club 824

  5+ Interested
• Sat, 17 Jan, 2026 - 08:00 PM

  Collin Raye in Winchester

  Backseat Events
• Sat, 06 Dec, 2025 - 06:00 PM

  Raziel & Hekate: Working with Witch Spirits

  105 Millwood Ave, Winchester, VA, United States, Virginia 22601

  12+ Interested
• Fri, 30 Jan, 2026 - 06:00 PM

  Karaoke at West Oaks

  4305 Middle Road, Winchester, VA, United States, Virginia 22602

  16+ Interested
• Sat, 13 Dec, 2025 - 05:30 PM

  Phil Kline’s Unsilent Night

  1460 University Dr, Winchester, VA, United States, Virginia 22601
• Wed, 31 Dec, 2025 - 08:00 PM

  Blues, Brass & Bubbly: A New Year’s Eve with Terry Oates & The Mudcats

  114 Full House Drive, Winchester, VA

  126+ Interested
• Fri, 05 Dec, 2025 - 07:00 PM

  Shockwave Band

  215 E Cork St, Winchester, VA
• Sat, 27 Dec, 2025 - 08:00 PM

  Cumberland Road at Bright Box Theater!

  Bright Box Theater

  33+ Interested
• Thu, 11 Dec, 2025 - 07:00 PM

  Swing into the Holidays with Winchester Swing Dance

  Shenandoah University Hazel Pruitt Armory, 608 Millwood Ave, Winchester, VA 22601

  55+ Interested
• Fri, 05 Dec, 2025 - 08:00 PM

  The Local Honeys / Ramona & The Holy Smokes / Rebecca Porter / Abby Hamilton

  Bright Box Theater

  9+ Interested
• Fri, 12 Dec, 2025 - 06:30 PM

  Classic French Holiday Dinner

  27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

  10+ Interested
• Sat, 20 Dec, 2025 - 06:00 PM

  8ball Chip Tournament

  109 Fullhouse Dr, Winchester, Va, 22603

  6+ Interested
• Sat, 06 Dec, 2025 - 11:00 AM

  Practical Tai Chi

  116 S Loudoun St, Winchester, VA 22601-4722, United States
• Sat, 03 Jan, 2026 - 07:00 PM

  Chuggalug at our fav Winchester Elks!

  Fraternal Order of Elks Lodge 867

  10+ Interested
• Sat, 13 Dec, 2025 - 11:00 AM

  Handley Library Tour - Behind the Scenes

  100 W Piccadilly St, Winchester, VA, United States, Virginia 22601

  6+ Interested
• Sat, 13 Dec, 2025 - 12:00 PM

  The Santa's Express Old Town Cookie Crawl

  Old Town Winchester Walking Mall
• Sat, 06 Dec, 2025 - 09:30 AM

  Beginners Yang-style Tai Chi

  116 S Loudoun St, Winchester, VA 22601-4722, United States
• Sat, 13 Dec, 2025 - 07:00 PM

  "Clue Christmas" - A Murder Mystery Comedy Show // 7PM SHOW

  Bright Box Theater

  14+ Interested
• Sat, 06 Dec, 2025 - 10:00 AM

  Library Shop Sale @ Handley Library

  100 W Piccadilly St, Winchester, VA, United States, Virginia 22601

  4+ Interested
• Sat, 24 Jan, 2026 - 07:00 PM

  Rosie Soul Returns to the Blue Fox!

  Blue Fox Billiards

  86+ Interested
• Sat, 09 May, 2026 - 10:00 AM

  Beltane Luna Market 2026

  125 S. Loudoun Street, Winchester, VA

  108+ Interested
• Fri, 12 Dec, 2025 - 05:00 PM

  December Friday² Free BEER & WINE Tasting + Pop Up Market

  90 Featherbed Ln, Winchester, VA
• Sat, 24 Jan, 2026 - 07:00 PM

  Winchester Elks Lodge - Mack Berry Band

  Elks Club

  8+ Interested
• Sat, 06 Dec, 2025 - 02:00 PM

  Poinsettia Dish garden Workshop

  1912 Martinsburg Pike, Winchester, VA

  34+ Interested
• Fri, 16 Jan, 2026 - 07:00 PM

  Collin Raye

  Backseat Events
• Sat, 13 Dec, 2025 - 02:00 PM

  Literacy Family Holiday Party with Santa

  Winchester Public Schools

  17+ Interested
• Sat, 20 Jun, 2026 - 10:00 AM

  Litha Luna Market 2026

  125 S. Loudoun Street, Winchester, VA

  63+ Interested
• Sat, 06 Dec, 2025 - 02:00 PM

  Poetry reading for Hanging the Angels

  Winchester Book Gallery

  6+ Interested
• Fri, 19 Dec, 2025 - 08:00 PM

  Big Hair, Bright Lights & Spank the 80s!

  114 Full House Drive, Winchester, VA

  197+ Interested
• Sat, 06 Dec, 2025 - 07:00 PM

  Breach The Silence, Sonic Disciple, 9 Realms @Granny's

  Granny's Place

  87+ Interested
• Sat, 20 Dec, 2025 - 04:30 PM

  Christmas Dinner and The Dixie Moon Band

  1730 Berryville Pike, Winchester, VA

  12+ Interested
• Sat, 06 Dec, 2025 - 10:00 AM

  Wicked Cookie Class

  The Typewriter Studio

  5+ Interested
• Sat, 20 Dec, 2025 - 10:00 AM

  A Day in the Kitchen: Advanced Macaron

  27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

  4+ Interested
• Sat, 06 Dec, 2025 - 01:00 PM

  New Construction - Sovereign Village, Winchester, VA

  253 Rossman Blvd Winchester, VA 22602
• Sat, 13 Dec, 2025 - 12:00 PM

  Santa Express

  231 E Piccadilly St, Winchester, VA, 22601

  14+ Interested
• Sat, 06 Dec, 2025 - 12:00 PM

  Champagne Saturday Class at Briedé Family Vineyards

  Briedé Family Vineyards
• Fri, 05 Dec, 2025 - 04:00 PM

  Friday Night Wine Tasting With Lori at The Beer & Wine Depot!

  1863 - A Berryville Pike, Winchester, VA
• Sat, 28 Feb, 2026 - 08:00 PM

  Shades of HUNKS at Winchester Brew Works (Winchester, VA) 02/28/26

  Winchester Brew Works

  USD 18
• Wed, 31 Dec, 2025 - 06:00 PM

  Old Town Winchester New Year's Eve Celebration 2026

  Old Town, Winchester

  141+ Interested
• Fri, 23 Jan, 2026 - 06:00 PM

  Vision & Vino: A Vision Board Social - TICKET NEEDED

  2 N Kent St, Winchester, VA 22601-5038, United States
• Fri, 23 Jan, 2026 - 08:00 PM

  Emo Night Karaoke 1/23 @ Bright Box Theater

  Bright Box Theater

  USD 21
• Fri, 16 Jan, 2026 - 06:00 PM

  Steak Dinner & Live Music from Those 3 Guys

  4305 Middle Road, Winchester, VA, United States, Virginia 22602
• Thu, 15 Jan, 2026 - 07:00 PM

  Wait Until Dark

  Winchester Little Theatre
• Sat, 13 Dec, 2025 - 02:00 PM

  Kid’s Christmas Party!

  1730 Berryville Pike

  5+ Interested
• Sat, 06 Dec, 2025 - 06:00 PM

  Christmas Tree Lighting

  4063 Middle Rd, Winchester, VA, United States, Virginia 22602

  87+ Interested
• Fri, 05 Dec, 2025 - 11:00 AM

  Diagnostic Ultrasound

  420 W Jubal Early Drive, Suite 105, Winchester, VA
• Sat, 20 Dec, 2025 - 08:00 PM

  Backseat Winchester Va

  Backseat Bar and Grill

  124+ Interested
• Thu, 11 Dec, 2025 - 05:00 PM

  Cow & Claus Ugly Sweater Party at Chick-fil-A

  2230 S Pleasant Valley Rd, 22601

  57+ Interested
• Sat, 07 Feb, 2026 - 06:00 PM

  Someone Special Dance

  West Oaks Farm Market

  26+ Interested
• Sat, 13 Dec, 2025 - 01:00 PM

  COCOA AND COOKIES WITH SANTA

  T-Bone's Bar & Grill

  46+ Interested
• Sun, 07 Dec, 2025 - 01:00 PM

  IN THE BELLY OF THE WHALE: part 2

  2139 Valley Ave
• Fri, 05 Dec, 2025 - 04:00 PM

  🍺 Tröegs Spotlight: Friday Beer Tastings at Shawnee Springs Market, Senseny Rd. 🍺

  Shawnee Springs Market & Cannery (Winchester, VA)

  14+ Interested
• Tue, 09 Dec, 2025 - 07:30 PM

  Keith Harkin Trio - Winchester VA Bright Box Theater

  Bright Box Theater

  11+ Interested
• Sat, 06 Dec, 2025 - 07:30 PM

  Choral Ensembles

  Armstrong Concert Hall
• Sat, 20 Dec, 2025 - 07:00 PM

  Dirty Santa Christmas Party!

  Broken Window Brewing Co.

  42+ Interested
• Thu, 11 Dec, 2025 - 06:00 PM

  Trans Family Affinity Group

  124 W Piccadilly St, Winchester, VA 22601-3916, United States
• Fri, 05 Dec, 2025 - 04:00 PM

  Fire Pit Fridays

  4063 Middle Rd, Winchester, VA, United States, Virginia 22602

  4+ Interested
• Sat, 13 Dec, 2025 - 10:00 AM

  Pictures with Santa @ West Oaks

  4305 Middle Road, Winchester, VA, United States, Virginia 22602

  1116+ Interested
• Sat, 06 Dec, 2025 - 12:00 PM

  Bake Sale ,get your holiday hugs with Santa and the Grinch!

  164 Poorhouse Rd, Winchester, VA, United States, Virginia 22602

  30+ Interested
• Sun, 07 Dec, 2025 - 12:00 PM

  Ornament Extravaganza

  157 N Loudoun St, Winchester, VA, United States, Virginia 22601

  10+ Interested
• Sun, 07 Dec, 2025 - 10:30 AM

  Worship Services — Winchester

  399 Apple Pie Ridge Rd, Winchester, VA, United States, Virginia 22603
• Fri, 05 Dec, 2025 - 12:00 PM

  Little Noon Music - Shenandoah Conservatory's Trombone Collective

  100 W Piccadilly St, Winchester, VA, United States, Virginia 22601

  8+ Interested
• Sun, 07 Dec, 2025 - 12:00 PM

  Readings With Chrystal

  105 Millwood Ave, Winchester, VA
• Sun, 07 Dec, 2025 - 10:00 AM

  Italia Performing Arts Institute GIFT WRAPPING FUNDRAISER

  Winchester Book Gallery

  14+ Interested
• Sat, 06 Dec, 2025 - 10:00 AM

  Marvelous Macaron

  27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

  89+ Interested
• Mon, 08 Dec, 2025 - 05:00 PM

  Adventures Through Grief - Winchester Teen Group

  314 Hope Dr, Winchester, VA 22601-6800, United States
• Sun, 04 Jan, 2026 - 12:00 PM

  Shark Pit 7-Year Anniversary Seminar

  210 Fort Collier Road, Unit 6, Winchester, VA

  91+ Interested
• Mon, 08 Dec, 2025 - 06:00 PM

  Holiday PJ Parties at WBW!

  320 N Cameron St, Winchester, VA

  9+ Interested
• Sat, 17 Jan, 2026 - 08:00 PM

  Wait Until Dark at Winchester Little Theatre Inc.

  Winchester Little Theatre Inc.
• Sat, 06 Dec, 2025 - 06:00 PM

  The Flying Ivories: Dueling Pianos (7PM SHOW) - ALL AGES

  Bright Box Theater

  5+ Interested
• Sun, 21 Dec, 2025 - 11:00 AM

  🎄 Christmas at Holy Ground Church ✨

  2908 Middle Road, Winchester, VA
• Sat, 13 Dec, 2025 - 06:00 PM

  Ugly Sweater Contest & Thieves Christmas!

  1730 Berryville Pike, Winchester, VA

  8+ Interested
• Fri, 12 Dec, 2025 - 08:00 PM

  The Bass Club Presents: MAD DUBZ

  Bright Box Theater

  USD 13
• Mon, 08 Dec, 2025 - 06:00 PM

  Loving Kindness Meditation with Adalaine Heartsong

  105 Millwood Ave, Winchester, VA, US
• Wed, 17 Dec, 2025 - 06:30 PM

  Christmas Music Bingo

  4305 Middle Road, Winchester, VA, United States, Virginia 22602

  416+ Interested
• Sat, 13 Dec, 2025 - 07:30 PM

  Flute Ensemble

  Goodson Chapel Recital Hall

  4+ Interested
• Sat, 10 Jan, 2026 - 08:00 PM

  The Amish Outlaws Return to Backseat Events in Winchester, VA

  114 Full House Drive , Winchester, VA, United States, Virginia 22603

  132+ Interested
• Fri, 05 Dec, 2025 - 05:00 PM

  ShenArts Holiday Market Opening Night

  128 N Loudoun St, Winchester, VA, United States, Virginia 22601

  39+ Interested
• Sun, 07 Dec, 2025 - 10:00 AM

  Elves Workshop

  19 W Cork St, Winchester, VA, United States, Virginia 22601

  41+ Interested
• Sat, 13 Dec, 2025 - 02:00 PM

  The Nutcracker Ballet

  John Handley High School

  16+ Interested
• Sat, 20 Dec, 2025 - 05:30 PM

  A DIVA's Christmas Special

  Bright Box (Winchester, VA)

  46+ Interested
• Sat, 13 Dec, 2025 - 04:15 PM

  Go Big and Stay Home

  Patti's Place

  USD 87
• Sun, 07 Dec, 2025 - 09:00 AM

  Worship Services — Shenandoah Valley

  The Church of Jesus Christ of Latter Day Saints
• Sat, 06 Dec, 2025 - 12:00 PM

  The Healing Breakthrough Live

  The Hilton Garden Inn
• Sun, 14 Dec, 2025 - 02:30 PM

  Van Buren Winds

  Armstrong Concert Hall